Synthesis of (±)-4,5-dia-Parthenolide, an Unnatural Parthenolide Stereoisomer

Freund, Robert R. A.; Arndt, Hans-Dieter

Synthesis of (±)-4,5-dia-Parthenolide, an Unnatural Parthenolide Stereoisomer

2016

Freund, Robert R. A. | Arndt, Hans-Dieter

A short total synthesis of the novel unnatural parthenolide diastereomer (±)-4,5-dia-parthenolide was accomplished in 13 steps and an overall yield of 1.75% starting from commercially available (E,E)-farnesol. The challenging isopropenyl side chain oxidation was regioselectively achieved via a newly developed stepwise dihydroxylation procedure, employing a Bartlett–Smith iodocarbonate cyclization followed by iodide substitution and catalytic transesterification.

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